5-[[3-(11,12-didehydrodibenz[b,f]azocin-5(6H)-yl)-3-oxopropyl]amino]-5-oxopentanoic acid | 1337920-25-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-[[3-(11,12-didehydrodibenz[b,f]azocin-5(6H)-yl)-3-oxopropyl]amino]-5-oxopentanoic acid
• 英文别名: 5-[[3-(2-azatricyclo[10.4.0.04,9]hexadeca-1(12),4(9),5,7,13,15-hexaen-10-yn-2-yl)-3-oxopropyl]amino]-5-oxopentanoic acid；ADIBO-carboxylic acid；Dbco-(CH2)2-NH2-CO-(CH2)3cooh；5-[[3-(2-azatricyclo[10.4.0.04,9]hexadeca-1(16),4,6,8,12,14-hexaen-10-yn-2-yl)-3-oxopropyl]amino]-5-oxopentanoic acid
• CAS: 1337920-25-8
• 化学式: C₂₃H₂₂N₂O₄
• 分子量: 390.439
• InChiKey: NSVCCHBUMXZEHM-UHFFFAOYSA-N

物化性质

• 沸点：
  774.6±60.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  86.7
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  5-[[3-(11,12-didehydrodibenz[b,f]azocin-5(6H)-yl)-3-oxopropyl]amino]-5-oxopentanoic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Sequential “Click” – “Photo-Click” Cross-Linker for Catalyst-Free Ligation of Azide-Tagged Substrates

  摘要：

  Heterobifunctional linker allows for selective catalyst-free ligation of two different azide-tagged substrates via strained-promoted azide-alkyne cycloaddition (SPAAC). The linker contains an azadibenzocyclooctyne (ADIBO) moiety on one end and a cyclopropenone-masked dibenzocyclooctyne (photo-DIBO) group on the other. The first azide-derivatized substrate reacts only at the ADIBO end of the linker as the photo-DIBO moiety is azide-inert. After the completion of the first SPAAC step, photo-DIBO is activated by brief exposure to 350 nm light from a fluorescent UV lamp. The unmasked DIBO group then reacts with the second azide-tagged substrate. Both click reactions are fast (k = 0.4 and 0.07 M(-1) s(-1), respectively) and produce quantitative yield of ligation in organic solvents or aqueous solutions. The utility of the new cross-linker has been demonstrated by conjugation of azide functionalized bovine serum albumin (azido-BSA) with azido-fluorescein and by the immobilization of the latter protein on azide-derivatized silica beads. The BSA-bead linker was designed to incorporate hydrolytically labile fragment, which permits release of protein under the action of dilute acid. UV activation of the second click reaction permits spatiotemporal control of the ligation process.

  DOI：

  10.1021/jo500143v
• 作为产物：
  描述：

  戊二酸酐 、 氮杂二苯并环辛炔胺 以 二氯甲烷 为溶剂， 以86 %的产率得到5-[[3-(11,12-didehydrodibenz[b,f]azocin-5(6H)-yl)-3-oxopropyl]amino]-5-oxopentanoic acid
  参考文献：
  名称：

  [EN] IMIDAZO[4,5-c]QUINOLINE-4-AMINE COMPOUNDS AND CONJUGATES THEREOF, THEIR PREPARATION, AND THEIR THERAPEUTIC APPLICATIONS
  [FR] COMPOSÉS IMIDAZO[4,5-C]QUINOLÉINE-4-AMINE ET LEURS CONJUGUÉS, LEUR PRÉPARATION ET LEURS APPLICATIONS THÉRAPEUTIQUES

  摘要：

  SANOFI "IMIDAZO[4,5-c]QUINOLINE-4-AMINE COMPOUNDS AND CONJUGATES THEREOF, THEIR PREPARATION, AND THEIR THERAPEUTIC APPLICATIONS" The present disclosure relates to compounds of formula (I) (I) wherein n is an integer from 1 to 50; R1 represents a hydrogen atom, a -(C1-C6)alkylene-O-(C1-C6)alkyl group, a -(C1-C6)alkylene-NH-(C1-C6)alkyl group, or a -(C1-C6)alkyl group; R2 represents a -(C1-C6)alkylene- group; R3 represents -O-, -NH- or a -N((C1-C6)alkyl)- group; R4 represents a hydrogen atom, a -(C1-C6)alkyl group or a -(C1-C6)alkoxy group; R5 represents a -(C1-C6)alkylene- group; and R6 represents a -L1-RCG1 group or a -RCG1 group. The present disclosure also relates to conjugates of formula (II), to processes for their preparation, to compositions comprising them and to their therapeutic uses, especially in the prevention and/or in the treatment of a disease or a disorder that may benefit of an activation of the immune system, such as cancers.

  公开号：

  WO2023057564A1

文献信息

• [EN] CONTROLLED DRUG RELEASE FROM SOLID SUPPORTS<br/>[FR] SUPPORTS SOLIDES POUR LA LIBÉRATION CONTRÔLÉE DE MÉDICAMENTS
  申请人：PROLYNX LLC

  公开号：WO2011140392A1

  公开（公告）日：2011-11-10

  The invention relates to solid supports useful in medical applications that provide controlled release of drugs, such as peptides, nucleic acids and small molecules. The drugs are covalently coupled to the solid support through a linkage that releases the drug or a prodrug through controlled beta elimination.

  这项发明涉及在医疗应用中有用的固体支持物，可提供药物的控制释放，如肽、核酸和小分子。这些药物通过一个通过受控β消除释放药物或前药的连接与固体支持物共价偶联。
• Attach, Remove, or Replace: Reversible Surface Functionalization Using Thiol–Quinone Methide Photoclick Chemistry
  作者：Selvanathan Arumugam、Vladimir V. Popik

  DOI：10.1021/ja302970x

  日期：2012.5.23

  of irradiation, thus allowing for the spatial control of the surface derivatization. A two-step procedure was employed for protein patterning: photobiotinylation of the surface with an NQMP-biotin conjugate followed by staining with FITC-avidin. The orthogonality of oNQM-thiol and azide click chemistry allowed for the development of a sequential click strategy, which might be useful for the immobilization

  光化学生成的邻萘醌甲基化物 (oNQM) 和硫醇之间非常容易发生反应，用于可逆光定向表面衍生化和图案化。硫醇官能化的载玻片上覆盖有与 3-(羟甲基)-2-萘酚 (NQMP) 缀合的底物的水溶液。随后通过荫罩进行照射，导致暴露区域中的 NQMP 有效转化为活性 oNQM 物质。后者与表面上的硫醇基团反应，在基材和表面之间产生硫醚连接。未反应的 oNQM 基团快速水合以再生 NQMP。oNQM 在水溶液中的寿命较短，阻止其从照射部位迁移，从而可以对表面衍生化进行空间控制。蛋白质图案化采用两步程序：用 NQMP-生物素缀合物对表面进行光生物素化，然后用 FITC-亲和素染色。oNQM-硫醇和叠氮点击化学的正交性允许开发连续点击策略，这可能对光敏化合物的固定有用。oNQM 和硫醇反应产生的硫醚键在环境条件下是稳定的，但可以通过紫外线照射裂解，重新生成游离硫醇。此功能允许移除或更换固定的基质。
• METHODS FOR LABELING A SUBSTRATE HAVING A PLURALITY OF THIOL GROUPS ATTACHED THERETO
  申请人：Boyd Graduate Studies Research Center University of Georgia Research Foundation, Inc.

  公开号：US20130281656A1

  公开（公告）日：2013-10-24

  Methods for derivatizing the surface of a substrate having a plurality of thiol groups thereon are disclosed herein. The method can include reacting the thiol groups with an o-quinone methide, which can optionally be generated by irradiating an o-quinone methide precursor compound. In some embodiments, the method can advantageously be reversible. Exemplary o-quinone methides having a cyclic alkyne attached thereto, and precursor compounds for generating such compounds, are also disclosed herein.

  本文揭示了一种衍生化具有多硫基团的基底表面的方法。该方法可以包括使用邻醌甲醚反应硫基团，该邻醌甲醚可以选择通过照射邻醌甲醚前体化合物来生成。在某些实施例中，该方法可以具有可逆性。本文还揭示了具有环状烷基连接的示例邻醌甲醚及用于生成这种化合物的前体化合物。
• CONTROLLED RELEASE FROM SOLID SUPPORTS
  申请人：Ashley Gary

  公开号：US20130123487A1

  公开（公告）日：2013-05-16

  The invention relates to solid supports useful in medical applications that provide controlled release of drugs, such as peptides, nucleic acids and small molecules. The drugs are covalently coupled to the solid support through a linkage that releases the drug or a prodrug through controlled beta elimination.

  本发明涉及固体支持在医学应用中的使用，提供药物的控制释放，例如肽、核酸和小分子。药物通过一个连接环节共价耦合到固体支持上，通过受控的β消除释放药物或前药。
• Cryptophycin antibody conjugates for the treatment of cancer
  申请人：SANOFI

  公开号：US11007275B2

  公开（公告）日：2021-05-18

  The present disclosure relates to compounds of formula (V): wherein Ab represents an antibody. The disclosure also relates to cryptophycin payloads, as well as to cryptophycin conjugates, to compositions containing them and to their therapeutic use, especially as anticancer agents. The disclosure also relates to the process for preparing these conjugates.

  本公开涉及式（V）化合物： 其中 Ab 代表抗体。本公开还涉及隐球菌苷有效载荷、隐球菌苷共轭物、含有它们的组合物及其治疗用途，特别是作为抗癌剂。本公开还涉及制备这些共轭物的工艺。